Methyl iodide → HCID 71523378, compound

HRID 2358903Notes

Reaction equation

HRID 2358903 reaction equation
[CH:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([O:8][CH:9]([CH3:19])[CH2:10][N:11]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:12])=[O:7])([CH3:3])[CH3:2].[CH3:24][I:25]>ClCCCl>[I-:25].[CH:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([O:8][CH:9]([CH3:19])[CH2:10][N+:11]([CH3:24])([CH3:12])[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:7])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86681544HCID 86681544, compound

Product 1

HCID 71523378HCID 71523378, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 1-(cyclohexyl(methyl)amino)propan-2-yl 2-isopropylbenzoate (0.45 g, 1.41 mmol) in DCE (3 mL) was added methyl iodide (0.35 mL, 5.67 mmol) and the reaction mixture was stirred at rt for 16 hours in a sealed tube. The reaction mixture was concentrated and the crude material was purified by Combiflash® chromatography, eluting with 3-4% CH3OH/DCM to provide a solid which was crystallized from methanol-ether to provide white N-[2-((2-isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide. Yield: 0.415 g (64%). 1H NMR (DMSO-d6) δ 7.71 (d, J=8 Hz, 1 H), 7.58-7.50 (m, 2 H), 7.31 (t, J=7 Hz, 1 H), 5.57-5.54 (m, 1 H), 3.93-3.87 (m, 1 H), 3.67-3.57 (m, 2 H), 3.38-3.34 (m, 1 H), 3.05 (s, 3 H), 3.02 (s, 3 H), 2.17-2.08 (m, 2 H), 1.87-1.84 (m, 1 H), 1.75-1.72 (m, 1 H), 1.54-1.42 (m, 3 H), 1.40 (d, J=6 Hz, 3 H), 1.24-1.19 (m, 7 H), 1.13-0.99 (m, 2 H). LCMS: m/z=332.0 [M+], RT=3.01 min, (Column: Y, Program: P1). UPLC: 98.43% (200 nm), RT=3.60 min (Mobile Phase A. 0.05% TFA in water, B. Acetonitrile; Column: Zorbax® SB-C18 (4.6×50 mm) 1.8μ)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude material was purified by Combiflash® chromatography
  3. washeluting with 3-4% CH3OH/DCM
  4. customto provide a solid which
  5. customwas crystallized from methanol-ether

Sources & evidence

ORD record
ord-c924383eb9b64ec6aa4c980dc1bd82a0
Source dataset
uspto-grants-2014_04
Patent number
US08685418B2

Reaction notes

Loading…